无过渡金属或无光催化剂条件下可见光促进喹喔啉酮C(3)—H官能团化研究进展

doi:10.6023/cjoc202307016

摘要/Abstract

喹喔啉酮及其衍生物是一类重要的含氮杂环化合物, 这种特殊的杂环骨架广泛存在于各种天然产物、药物分子以及功能材料中. 近年来, 喹喔啉酮的官能团化引起了化学工作者的广泛关注, 其中通过C—H官能团化构建3-官能团化的喹喔啉酮取得了重要进展. 光氧化还原催化可利用绿色清洁的光能在较为温和的条件下实现有机化合物的合成与转化, 因此, 越来越多的光催化体系被开发用于喹喔啉酮的官能团化. 简单高效的无过渡金属或无光催化剂的反应体系非常符合绿色化学和可持续发展的要求, 已成为喹喔啉酮类化合物官能团化强有力的工具, 同时也受到了很多学者的青睐. 对近五年来无过渡金属或无光催化剂可见光促进喹喔啉酮的C(3)位官能团化领域所取得的研究进展进行了综述, 对反应机理和氧化还原淬灭过程进行了总结, 并对该领域所面临的挑战和机遇进行了展望和探讨.

关键词: 喹喔啉酮, 光氧化还原, 无过渡金属, 无光催化剂, C—H官能团化

Quinoxalinone and its derivatives are significant non-aromatic heterocycles existing in various bioactive natural products, pharmaceuticals, and functional materials, and exhibit an impressive spectrum of important biological properties. In recent years, the functionalization of quinoxalinones has attracted extensive attention of chemical workers, and important progress has made in the construction of C-3 substituted quinoxalinones by C—H functionalization. Photoredox catalysis has been widely used in the synthesis and conversions of organic compounds, because it can generate high reactive free radical intermediates under mild conditions using green and clean energy. Thus, photocatalysis synthesis is becoming powerful tools for C—H functionalization of quinoxalinone. This photocatalytic reactions under transition-metal-free or photocatalyst-free conditions meet the requirements of green chemistry and sustainable development, which have become a powerful tool for the functionalization of quinoxalinones and attracted the attention of many scholars. The research progress of C(3)—H functionalization of quinoxalinones by visible-light photoredox catalysis under transition-metal-free or photocatalyst-free conditions is reviewed during the past five years. The reaction mechanisms are systematically discussed, and the challenges and opportunities of this field are included.

Key words: quinoxalinone, photoredox, transition-metal-free, photocatalyst-free, C—H functionalization

引用此文

董江湖, 宣良明, 王池, 赵晨熙, 王海峰, 严琼姣, 汪伟, 陈芬儿. 无过渡金属或无光催化剂条件下可见光促进喹喔啉酮C(3)—H官能团化研究进展[J]. 有机化学, 2024, 44(1): 111-136.

Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.

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图/表 45

图1. 具有生物活性的3-取代喹喔啉酮

Figure 1. Selected bioactive C(3)-substituted quinazolinones

图2. 常见有机光敏剂结构

Figure 2. Structures of common organic photocatalysts

图式1. 无过渡金属可见光促进喹喔啉酮C(3)位官能团化的两种反应途径

Scheme 1. Two reaction pathways of C(3) functionalization of quinazolinones under visible-light-induced transition-metal-free conditions

图式2. 可见光促进喹喔啉酮与醚的直接C—H/C—H交叉偶联反应

Scheme 2. Visible-light-promoted direct C—H/C—H cross-coupling reaction of quinazolinones with ethers

图式3. 可见光促进喹喔啉酮与醚的交叉偶联反应

Scheme 3. Visible-light-promoted cross-coupling reaction of quinazolinones with ethers

图式4. 光催化喹喔啉酮与环丁酮肟酯的氰烷基化反应

Scheme 4. Photocatalytic cyanoalkylation of quinazolinones with cyclobutanone oxime esters

图式5. 可见光诱导氨基酸的脱羧杂芳香化反应

Scheme 5. Visible-light-promoted decarboxylative heteroarylation of amino acids

图式6. 可见光诱导杂环芳烃的直接烷基化反应

Scheme 6. Visible-light-induced direct alkylation of heteroaromatics

图式7. 光催化喹喔啉酮与溴二氟酰胺的分子内环化/烷基化反应

Scheme 7. Photocatalytic intramolecular cyclization/alkylation of quinazolinones with bromodifluoroacetamides

图式8. 无过渡金属光催化喹喔啉酮的苄基化反应

Scheme 8. Transition metal-free photocatalytic benzylation of quinazolinones

图式9. 可见光促进喹喔啉酮的C—H苄基化反应

Scheme 9. Visible-light induced C—H benzylation of quinazolinones

图式10. 光催化Katritzky盐和喹喔啉酮的C-3烷基化

Scheme 10. Photocatalytic C-3 alkylation of Katritzky salt and quinazolinones

图式11. 无过渡金属可见光诱导喹喔啉酮缩醛化反应

Scheme 11. Transition-metal-free visible-light-induced acetalization of quinazolinones

图式12. 可见光促进喹喔啉酮的芳基化反应

Scheme 12. Visible-light-driven arylation of quinazolinones

图式13. 可见光诱导喔啉酮与吡咯衍生物的氧化偶联反应

Scheme 13. Visible-light-induced oxidative coupling reaction of quinazolinones with pyrrole derivatives

图式14. 光催化α-氧代羧酸与喹喔啉酮的脱羧酰化反应

Scheme 14. Photocatalytic decarboxylative acylation of α-oxocarboxylic acids with quinazolinones

图式15. 可见光光催化喹喔啉酮与醛的C—H酰化反应

Scheme 15. Visible-light photocatalytic C—H acylation of quinazolinones with aldehydes

图式16. 可见光促进喹喔啉酮与胺的C—N交叉偶联反应

Scheme 16. Visible-light-promoted C—N cross-coupling reaction of quinazolinones with amines

图式17. 光催化喹喔啉酮与苯并三唑的芳胺化反应

Scheme 17. Photocatalytic arylamination of quinazolinones with benzotriazoles

图式18. 可见光促进喹喔啉酮与醇的C—H/O—H脱氢偶联反应

Scheme 18. Visible-light-driven C—H/O—H dehydrogenative coupling reaction of quinazolinones with alcohols

图式19. 可见光促进二氧化硫的多组分插入反应

Scheme 19. Visible-light-promoted sulfur dioxide insertion reaction of multi components

图式20. 光诱导喹喔啉酮、烯烃与三氟甲基亚磺酸钠或亚磺酸的三组分串联反应

Scheme 20. Photoinduced three-component tandem reaction of quinazolinones, olefins with sodium trifluoromethylsulfinates or sulfinic acids

图式21. 光催化喹喔啉酮的三组分偶联反应

Scheme 21. Photocatalytic three-component coupling reaction of quinazolinones

图式22. 可见光光氧化还原催化喹喔啉酮的磷酸化

Scheme 22. Visible light photoredox-catalyzed phosphorylation of quinazolinones

图式23. 可见光促进喹喔啉酮与硫醇的C—S交叉偶联反应

Scheme 23. Visible-light-promoted C—S cross-coupling reaction of quinazolinones with thiols

图式24. 光氧化还原催化喹喔啉酮或缺电子杂芳烃的C—H硅烷化反应

Scheme 24. Photoredox-catalyzed C—H silylation of quinoxalinones or electron-deficient heteroarenes

图式25. 可见光促进喹喔啉酮C(3)烷基化和芳基化反应

Scheme 25. Visible-light-driven C(3) alkylation and arylation of quinazolinones

图式26. 光催化喹喔啉酮的三氟烷基化和三氟烯基化反应

Scheme 26. Photocatalytic trifluoroalkylation and trifluoroalkenylation of quinazolinones

图式27. 可见光促进喹喔啉酮的硫醇化反应

Scheme 27. Visible-light-driven thiolation of quinazolinones

图式28. 氧掺杂石墨氮化碳促进喹喔啉酮与芳基重氮盐的芳基化反应

Scheme 28. OCN promoted the arylation reaction of quinoxalinone with aryl diazonium salts

图式29. 光催化下喹喔啉酮与芳基肼的芳基化反应

Scheme 29. Photocatalytic arylation of quinazolinones with arylhydrazines

图式30. 可见光催化喹喔啉酮与硫醇的交叉脱氢偶联反应

Scheme 30. Visible-light-promoted cross-dehydrogenative coupling reaction of quinoxalinone with thiols

图式31. 光催化喹喔啉酮的C(3)—H烷基化反应

Scheme 31. Photocatalytic C(3)—H alkylation of quinazolinones

图式32. 光催化喹喔啉酮与芳酰基过氧化物直接C—H芳基化反应

Scheme 32. Photocatalytic direct C—H arylation of quinazolinones with aroyl peroxides

图式33. 光催化喹喔啉酮的酰胺化反应

Scheme 33. Photocatalytic amidation of quinazolinones

图式34. 可见光促进喹喔啉酮与烯烃和二氟碘试剂的三组分二氟烷基化反应

Scheme 34. Visible-light-promoted three-component difluoroalkylation of quinoxalinones, olefins and difluoroiodine reagents

图式35. 光催化N-杂环芳烃的芳基化反应

Scheme 35. Photocatalytic the arylation reaction of N-heterocyclic compounds

图式36. 光催化盐酸介导喹喔啉与芳肼的C(3)—H芳基化反应

Scheme 36. Photocatalytic hydrochloric acid-mediated C(3)—H arylation of quinoxalines with arylhydrazines

图式37. 可见光促进喹喔啉酮与烯烃和芳基二硫化物的硫代烷基化反应

Scheme 37. Visible light promoted thioalkylation of quinoxalinones with olefins and aryl disulfides

图式38. 光催化N-氟代酰胺与喹喔啉酮的远端C(sp3)—H杂芳基化反应

Scheme 38. Photocatalytic remote C(sp3)—H heteroarylation of N-fluorocarboxamides with quinazolinones

图式39. 无光催化剂的光催化喹喔啉酮烷基化反应和氧化反应

Scheme 39. Photocatalytic alkylation and oxidation of quinazolinones under photocatalyst-free conditions

图式40. 光催化喹喔啉酮和脂肪醛的脱羰基C—H烷基化反应

Scheme 40. Photocatalytic decarbonylative C—H alkylation of quinazolinones with aliphatic aldehydes

图式41. 可见光诱导NHPI酯和喹喔啉酮直接脱羧偶联

Scheme 41. Visible-light-driven direct decarboxylative coupling reaction of NHPI esters with quinazolinones

图式42. 光催化喹喔啉酮与Katritzky盐烷基化反应

Scheme 42. Photocatalytic alkylation between quinazolinones and Katritzky salts

图式43. 可见光促进N-烯丙基溴二氟酰胺与喹喔啉酮的自由基环化/杂芳基化串联反应

Scheme 43. Visible-light-promoted tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinazolinones

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